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Choose from 2984 Chester Hotel Deals

Fullerton Inn
Reviewed on Jul 13, 2025

Woodstock Inn & Resort
Reviewed on Jul 13, 2025

Colonial Motel And Spa
Reviewed on Jul 14, 2025

Kimpton Taconic Hotel by IHG
Reviewed on Jun 20, 2025

The Equinox Golf Resort & Spa
Reviewed on Jul 14, 2025

The Shire Woodstock
Reviewed on Jul 10, 2025

Hampton Inn Brattleboro
Reviewed on Jul 11, 2025

Latchis Hotel
Reviewed on Jul 4, 2025

On The River Inn
Reviewed on Jul 13, 2025

Comfort Inn & Suites Brattleboro I-91
Reviewed on Jul 13, 2025

Best Western Plus Keene Hotel
Reviewed on Jul 6, 2025

Hampton Inn and Suites Manchester
Reviewed on Jul 15, 2025
Find cheap hotels in Chester
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For you, intrepid voyager, Hotwire has a large selection of the best hotels in Chester.
Choosing the right hotel in Vermont has everything to do with the way you want your trip to go. If you’ve scribbled a few obscure destinations on your itinerary, you probably already have a good sense of how your getaway is taking shape. Lean into that by booking one of Chester’s 2,984 hotels. Choose the one that best catches your trip’s tourist drift.
If you’re traveling during the week for business, Hotwire can score you a luxury hotel for as low as $120. In town for pleasure? Hotwire still has you covered. If you’re in the mood for a quick last-minute weekend getaway or spa retreat, you can get great Chester hotel deals at the last minute.
While traveling, where you stay plays a major role in your overall vacation enjoyment. Choosing the right hotel is just as important as making sure you book the right flight and car rental. If you’re traveling with family or friends, you may need to book a hotel with connecting rooms. If you enjoy an elegant and relaxing hotel ambiance, opt for one of Hotwire’s luxury hotels in Chester. No matter your reason for visiting Chester, with Hotwire’s large selection of hotels in the area, you’re sure to book a hotel that meets all your accommodation needs.
Frequently Asked Questions About Chester hotels
Where can I find the best last-minute travel deals?
If you’re traveling in the spirit of spontaneity, you’ll love the idea of leaving your exact hotel choice up to chance. With Hotwire Hot Rates, you can unlock great deals on your next flight, hotel, or car rental. Just plug in your general preferences and let Hotwire choose last-minute hotel deals in Chester for as low as $120.
How many hotels are there in Chester?
With over 2,984 hotels in Chester, you’re sure to find one that best matches your travel mood. When you book with Hotwire, you can score a stellar home away from home for as low as $120.
How to find cheap car rentals in Chester?
Finding a cheap car rental deal in Chester is as easy as scoring cheap hotels in Chester. Hotwire partners with top-of-the-line car rental companies to bring you a large selection of affordable options. Whether you’re in need of a large SUV for the entire family or a more compact but stylish vehicle, Hotwire has you covered. You can unlock great car rental deals if you book a Hotwire Hot Rate at the last minute.
Top Booked Hotels in Chester
- Woodstock Inn & Resort
- Colonial Motel And Spa
- Kimpton Taconic Hotel by IHG
- The Equinox Golf Resort & Spa
- Hampton Inn Brattleboro
- Latchis Hotel
- Comfort Inn & Suites Brattleboro I-91
- Best Western Plus Keene Hotel
- Hampton Inn and Suites Manchester
- The Covered Bridge Inn
- Keene Elm City Hotel, Ascend Hotel Collection
- Hotels near DaVallia Art & Accents
- Hotels near Bonnie's Bundles Dolls
- Hotels near Okemo Mountain Resort
- Hotels near Stratton Mountain Resort
- Hotels near Mount Snow
- Hotels near Killington Resort
- Hotels near Green Mountain National Forest
- Hotels near Bromley Mountain Ski Resort
- Hotels near Magic Mountain Ski Resort
- Hotels near Keene State College
- Hotels near Connecticut River
- Hotels near Golf Club at Equinox
- Hotels near Vermont Country Store
- Hotels near Equinox Preservation Trust
- Hotels near Mount Ascutney
- Hotels near Stratton Mountain Summit Gondola
- Hotels near Hildene
- Hotels near Billings Farm and Museum
- Hotels near Connecticut Lakes Region
- Hotels near Mount Snow Golf Course
- Woodstock Hotels
- White Mountains Hotels
- Killington Hotels
- Manchester Hotels
- Brattleboro Hotels
- Keene Hotels
- White River Junction Hotels
- Rutland Hotels
- Manchester Center Hotels
- Ludlow Hotels
- Quechee Hotels
- West Lebanon Hotels
- West Dover Hotels
- Wilmington Hotels
- Stratton Hotels
- Appalachian Mountains Hotels
- Londonderry Hotels
- Cavendish Hotels
- Weston Hotels
- Dorset Hotels